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Rosenberg is known for his controversial and sarcastic humor as a host on many radio stations including, WAXY "790 The Ticket" in Miami, where he hosted his own morning show. He originally was paired with O.J. McDuffie, formerly a wide receiver with the Miami Dolphins; McDuffie resigned his position with the station in the summer of 2006.
Rosenberg's self-given jokingly middle name "Arthur" is a reference to former baseball player Dave Kingman. When Hall of Fame sportscaster Bob Murphy gave the lineups for the New York Mets, he would always give Kingman's name as "David Arthur Kingman"; Rosenberg continues this running gag on the Sports Guys by using Arthur as everybody's middle name.
His radio career started in West Palm Beach, Florida, where he hosted the syndicated sports radio program The Drive on Sports Fan Radio Network in the late 1990s, after starting as an Internet broadcast. In 2000, he moved to New York City to co-host WNEW-FM's turbulent morning show, the Sports Guys. A year later, he joined the Imus in the Morning program. He shared the sports broadcasting duties with Warner Wolf before becoming the full-time sports reporter. He engaged in heated half-mock, half-serious disputes with the other members of the Imus cast, leading for example to an actual boxing bout with producer Bernard McGuirk. Several months after joining the Imus show, he became the co-host of the midday show on Imus' flagship station, WFAN. Here, his strong knowledge of sports and distinctive, high-pitched Brooklyn accent served him well. He would hold both broadcasting positions until 2005. For several years, he also hosted the radio pre-game shows for New York Giants home games.
Rosenberg was no stranger to controversy on the Imus show, which was also simulcast on MSNBC cable television, therein increasing his remarks' visibility. Among other things, he said on-air that Venus Williams was an "animal," and that she and Serena Williams would be better suited for National Geographic Magazine than for Playboy, that "faggots play tennis" and that the United States women's national soccer team were "a bunch of juiced up dykes." He referred to Palestinians as "stinking animals" and suggested that "They ought to drop the bomb right there, kill 'em all right now" during the November 12, 2004 funeral of deceased Palestinian Authority leader Yasser Arafat.
WFAN executives accepted Rosenberg's resignation September 12, 2005, following his failing to show up to host the New York Giants' pre-game show having made an appearance for FHM in Atlantic City, NJ the previous day.
Rosenberg returned to WFAN on Saturday February 6, 2010 to host a special Super Bowl preview show from Miami. On Saturday March 27, 2010 Rosenberg again returned to WFAN hosting a show in Port St. Lucie before the New York Mets faced the Washington Nationals. He also completed two weeks of fill-in work with Kimberly Jones, Marc Malusis and Anita Marks on WFAN in July 2010 from 10 a.m to 1 p.m for Joe Benigno and Evan Roberts, who themselves were filling in for Mike Francesa from 1 p.m. to 6:30 p.m. WFAN's Mark Chernoff told Newsday of Long Island's Neil Best that he was very impressed with Sid's return to the FAN, but that there was very little he could do to make the temporary hosting in New York anything more than temporary.
In 2011, Rosenberg became the weekday morning sports anchor for WFAN's sister station, WINS. He left WINS in 2012.
Rosenberg returned to the airwave at WMEN 640AM on August 13, 2012
He and his wife Danielle were married in 1992 and have two children. Rosenberg, who is the cousin of former Minnesota senator Norm Coleman, attended the University of Miami and Brooklyn College in 1984 and 1985 but dropped out of both. He then got an associates degree from Kingsborough Community College in 1990 followed by a BA in Business from Baruch College in the Flatiron/Gramercy section of Manhattan in 1992.